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#158 | From Teenage Entrepreneur to the CTO: Building Teams That Win in the AI Era w/ Ben Wilcox @ProArch
Published 5 days, 6 hours ago
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▶︎ #158 | From Teenage Entrepreneur to the CTO: Building Teams That Win in the AI Era w/ Ben Wilcox @ProArch
In this episode of the Leman Tech Leadership Podcast, Alex welcomes Ben Wilcox: a CTO and CISO of ProArch, for a wide-ranging conversation about what it actually takes to lead technology teams in the age of AI. Ben's story is anything but conventional: he started monetising the internet as a 15-year-old, built and sold a web hosting business before most people his age had a bank account, and has spent the last 19 years growing from an individual contributor to holding two C-suite roles simultaneously.
Ben brings a rare perspective: one that sits at the intersection of deep technical expertise, security leadership, and people development. He started his career in Microsoft infrastructure and consulting, got into cloud migrations as early as 2008, and found his way into leadership not because he was chasing a title, but because he needed to "reproduce himself" at scale. That origin story shapes everything about how he leads today.
The conversation digs into some of the most pressing challenges facing tech leaders right now: how AI is forcing dev and security teams to finally, genuinely collaborate (not just claim they do); why the consultative mindset that got deprioritised during the post-COVID "ship it fast" era is now urgently needed again, but this time at speed; and how the shape of tech teams is changing, with junior roles evolving, the business analyst function making a comeback, and the mid-layer being pushed to add business context to stay relevant.
If you lead a team in technology (or you're thinking about making that move), this episode will give you both the strategic lens and the practical mindset to navigate what's coming next.
✔︎ Mentioned in the episode:
“People of the Deer”
✉︎ FOLLOW BEN ON: ⤵︎
LinkedIn: @ben-wilcox
ProArch: https://www.proarch.com
✉︎ FOLLOW ME ON: ⤵︎
LinkedIn: @aleksandralemanska
TikTok: @aleksandra_lemanska
X: @lemanskills
Startup Community Poznan: @startup-community-poznan-scp
www.lemanskills.com
Join Leadership Pulse! https://lemanskills.com/pulse/
In this episode of the Leman Tech Leadership Podcast, Alex welcomes Ben Wilcox: a CTO and CISO of ProArch, for a wide-ranging conversation about what it actually takes to lead technology teams in the age of AI. Ben's story is anything but conventional: he started monetising the internet as a 15-year-old, built and sold a web hosting business before most people his age had a bank account, and has spent the last 19 years growing from an individual contributor to holding two C-suite roles simultaneously.
Ben brings a rare perspective: one that sits at the intersection of deep technical expertise, security leadership, and people development. He started his career in Microsoft infrastructure and consulting, got into cloud migrations as early as 2008, and found his way into leadership not because he was chasing a title, but because he needed to "reproduce himself" at scale. That origin story shapes everything about how he leads today.
The conversation digs into some of the most pressing challenges facing tech leaders right now: how AI is forcing dev and security teams to finally, genuinely collaborate (not just claim they do); why the consultative mindset that got deprioritised during the post-COVID "ship it fast" era is now urgently needed again, but this time at speed; and how the shape of tech teams is changing, with junior roles evolving, the business analyst function making a comeback, and the mid-layer being pushed to add business context to stay relevant.
If you lead a team in technology (or you're thinking about making that move), this episode will give you both the strategic lens and the practical mindset to navigate what's coming next.
✔︎ Mentioned in the episode:
“People of the Deer”
✉︎ FOLLOW BEN ON: ⤵︎
LinkedIn: @ben-wilcox
ProArch: https://www.proarch.com
✉︎ FOLLOW ME ON: ⤵︎
LinkedIn: @aleksandralemanska
TikTok: @aleksandra_lemanska
X: @lemanskills
Startup Community Poznan: @startup-community-poznan-scp
www.lemanskills.com
Join Leadership Pulse! https://lemanskills.com/pulse/